4-Methyl-N-[4-(3-nitro-phenyl)-thiazol-2-yl]-benzenesulfonamide

ID: ALA136545

PubChem CID: 4233969

Max Phase: Preclinical

Molecular Formula: C16H13N3O4S2

Molecular Weight: 375.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(S(=O)(=O)Nc2nc(-c3cccc([N+](=O)[O-])c3)cs2)cc1

Standard InChI:  InChI=1S/C16H13N3O4S2/c1-11-5-7-14(8-6-11)25(22,23)18-16-17-15(10-24-16)12-3-2-4-13(9-12)19(20)21/h2-10H,1H3,(H,17,18)

Standard InChI Key:  CQTUVGBSDYRJEU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    6.7292   -0.5542    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.3167   -1.2750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4917   -1.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0125   -1.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917   -4.1750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2292   -1.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0125   -0.6125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.2292   -0.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917   -3.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4542   -0.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5125   -2.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1500    0.1625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0125   -0.1417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5125   -2.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0792   -4.5875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5125   -4.5875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1667   -0.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4542   -1.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1667   -2.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8792   -0.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8792   -1.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0792   -2.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917   -1.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0792   -2.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6042   -2.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  3  2  0
  5  9  1  0
  6  4  1  0
  7  3  1  0
  8  7  1  0
  9 14  2  0
 10  1  1  0
 11  6  1  0
 12  1  2  0
 13  1  2  0
 14 11  1  0
 15  5  1  0
 16  5  2  0
 17 10  1  0
 18 10  2  0
 19 18  1  0
 20 17  2  0
 21 19  2  0
 22 24  2  0
 23 11  2  0
 24 23  1  0
 25 21  1  0
 21 20  1  0
  8  6  2  0
  9 22  1  0
M  CHG  2   5   1  15  -1
M  END

Alternative Forms

1. Parent:

   

   ALA136545

   4-Methyl-N-[4-(3-nitro-phenyl)-thiazol-2-yl]-benzenesulfonamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 375.43

Molecular Weight (Monoisotopic): 375.0347

AlogP: 3.83

#Rotatable Bonds: 5

Polar Surface Area: 102.20

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.78

CX Basic pKa: ┄

CX LogP: 4.29

CX LogD: 3.75

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.54

Np Likeness Score: -2.31

References

1. Röver S, Cesura AM, Huguenin P, Kettler R, Szente A..  (1997)  Synthesis and biochemical evaluation of N-(4-phenylthiazol-2-yl)benzenesulfonamides as high-affinity inhibitors of kynurenine 3-hydroxylase.,  40  (26): [PMID:9435907] [10.1021/jm970467t]

Source

Source(1):

• Scientific Literature